Explore the walls of Monteriggioni in the early morning, and have the town to yourself. The intact walls are amazing, and inside is pretty: there’s a couple of cafes and the church of Santa Maria Assunta in the central piazza. Then, walk through shady woodland for the day towards Siena - it’s a secret, clandestine route into the city and a very cool way to arrive.
There are plenty of places to stay in Siena, including a pilgrim hostel at Casa delle Balie. Spend at least a day in the city, soaking in its extraordinary atmosphere. Make sure you visit Siena Cathedral of course: if the marble exterior impresses you the inside is even more astonishing, with its giant floor murals and starry night ceiling. It’s also where you collect your pilgrim stamp for your credential - pilgrims with one gain entry to the Cathedral for free.
Just opposite the Cathedral is Santa Maria della Scala, the old pilgrim stop and hospital, now an information centre. It’s a fascinating place to have a look in, and it now sells food and coffees.
Note that if you time your walk right, you could be in Siena for the Palio horse race, held twice a year in July and August. We’d recommend it as an incredible experience.
From here, catch a local bus to San Quirico d’Orcia, a gateway town to the most dreamy Tuscan countryside.
Check out here all the details about the leg from Monteriggioni to Siena.